1-Chloro-4-(chloromethyl)benzene → 2-Amino-7-(p-chloro-benzyl)-6,7,8,9-tetrahydro-5H-pyrazino[2,3-d]azepine

HRID 1153764Notes

Reaction equation

HRID 1153764 reaction equation
Br.Br.[NH2:3][C:4]1[CH:5]=[N:6][C:7]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9][C:8]=2[N:14]=1.C(N(C(C)C)C(C)C)C.[Cl:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Cl)=[CH:27][CH:26]=1>C(#N)C>[NH2:3][C:4]1[CH:5]=[N:6][C:7]2[CH2:13][CH2:12][N:11]([CH2:29][C:28]3[CH:31]=[CH:32][C:25]([Cl:24])=[CH:26][CH:27]=3)[CH2:10][CH2:9][C:8]=2[N:14]=1

Participants

5

Reactant 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 81531DiisopropylethylamineHCID 204363772-amino-6,7,8,9-tetrahydro-5H-pyrazino[2,3-d]azepine dihydrobromide

Product 1

HCID 130370462-Amino-7-(p-chloro-benzyl)-6,7,8,9-tetrahydro-5H-pyrazino[2,3-d]azepine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3.0 gm (9.2 mmols) of 2-amino-6,7,8,9-tetrahydro-5H-pyrazino[2,3-d]azepine dihydrobromide were suspended in 100 ml of acetonitrile, 7.5 ml of N-ethyl-diisopropylamine were added to the suspension, and the mixture was admixed dropwise with 1.5 gm (9.3 mmols) of p-chloro-benzyl-chloride. The reaction mixture was stirred for 48 hours and then evaporated, the residue was acidified with dilute hydrochloric acid, and the mixture was extracted with methylene chloride. The aqueous phase was made alkaline and then exhaustively extracted with methylene chloride, the extracts were evaporated, and the residue was column-chromatographically purified on silicagel with ethyl acetate as the mobile phase.

Workup

  1. customevaporated
  2. extractionthe mixture was extracted with methylene chloride
  3. extractionexhaustively extracted with methylene chloride
  4. customthe extracts were evaporated
  5. custompurified on silicagel with ethyl acetate as the mobile phase

Sources & evidence

ORD record
ord-e74a67af837d4dd68326f1f38487f1b6
Source dataset
uspto-grants-1984_12
Patent number
US04486433

Reaction notes

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